Wrestled Into Submission

It took less than an hour before the sun started rising outside her window. When she woke up groggily, she reached out instinctively to touch his hip. However, her hand met only empty space.

Her heart raced slightly as she turned quickly to look at the other side of the bed. There lay Benjamin, still sleeping soundly despite being tied to the bedposts again, this time upside down with arms and legs stretched above him. Of course he couldn't have moved.

A few inches below where his head rested upon the pillow, the base of his penis pressed firmly against the mattress. The slightest amount of movement caused him to grunt softly in pain. A moment later, he opened his eyes slowly to take in what happened during the night. Seeing Erica sitting up beside him, he looked surprised and embarrassed simultaneously.

"I... I'm sorry, Mistress," he stammered. Clearly he struggled to understand why she would have allowed him such liberties last night if he was supposed to remain obedient today.

"You're awake!" she exclaimed, laughing as she realized he must have been dreaming about their activities together. "You've already learned my name, Ben! You can call me Erica now."

His expression changed instantly when she said those words, and he nodded eagerly. "Yes, Erica!"

"Good boy." Her voice softened considerably compared to earlier. "Now let's get dressed and go eat something."

After showering together, they headed downstairs to the hotel dining room. Once seated, she ordered coffee and eggs Benedict for both of them. While waiting for their food, she pulled out her phone and sent a text message to her assistant: "I'll be back tomorrow morning. Please book me a flight home ASAP."

When the waiter arrived with their order, she noticed that Benjamin appeared nervous again. It wasn't just because he hadn't eaten anything since dinner yesterday; rather, he seemed worried that she might change her mind about allowing him to speak freely.

Erica decided to put his fears to rest by asking him several questions about himself. After learning that he worked as an accountant, she asked him whether he enjoyed numbers or preferred working with people more.

He answered honestly each question she posed, and she found herself enjoying listening to his responses.

In fact, she liked hearing him talk so much that she forgot entirely about the rules she set for him last night. Before she knew it, she had finished eating and was leaning forward towards him, eager to hear more about his life.

However, suddenly she remembered that she needed to keep things interesting. Otherwise, he wouldn't want to spend another evening with her. So she sat back in her chair and crossed her arms, looking sternly at him.

"What do you think is going to happen next?" she asked pointedly.

He hesitated briefly before answering, "well, I guess we could go shopping? Or maybe watch some movies?"

"Nope," she replied simply. "We're going to play a game called 'Truth or Dare.'"

He frowned slightly. "What does that mean?"

"It means you tell me three truths about yourself -- things nobody else knows -- then I will give you two dares to complete. If you refuse either dare, I will lock you inside a chastity device for twenty four hours without letting you cum."

She watched his face closely as she spoke.

The idea clearly terrified him, yet he also seemed excited by the prospect of revealing intimate details about himself. She wondered which one would win out.

"Okay..." he finally managed to say quietly. "But what happens if I succeed?"

"If you manage to finish both tasks successfully, then I'll allow you to choose your own reward."

He thought hard for a minute before speaking again. "And if I fail?"

Erica smiled wickedly. "Then I'll decide how long you stay locked away."

---

Back upstairs in her room, Erica waited patiently while Benjamin tried to figure out how best to begin. Finally, he cleared his throat nervously. "Well, um, I don't know exactly what kind of information you are expecting from me..."

She cut him off abruptly. "No need to worry, Ben. Just start talking."

He paused for a second longer before beginning. "Alright, well, I like to read books sometimes instead of watching TV."

"That doesn't count," she interrupted once again.

He sighed heavily but continued anyway. "Fine. Um, okay. Well, I used to work as a bartender until I got fired for not showing up on time too many times."

"And?"

"Well, I didn't show up on time because I was always late getting ready in the mornings due to having trouble waking up early enough."

"So you're lazy?"

"No, no, I'm not lazy! I just hate mornings."

"Is there any reason why you dislike them so much?"

"Not really. I just prefer staying up late and sleeping in whenever possible."

"Hmm, sounds like you'd make a good wrestler."

He blushed slightly. "Thanks, Erica."

She grinned. "That's number two. Now for number three."

He took a deep breath before continuing. "Um, well, I actually haven't told anyone this before, but I'm pretty sure I'm bisexual."

Her eyebrows shot up immediately. "Oh? Really?

Why did you wait so long to share that?"

He shrugged awkwardly. "It never came up before... And I figured you probably weren't interested in dating someone who isn't straight."

She laughed softly. "Not true. In fact, I find men who aren't afraid to explore all sides of themselves incredibly attractive. But I still don't understand why you kept quiet about it for so long."

"I've only been thinking about coming out recently. I wanted to make sure my family accepted me first before telling everyone else."

"Oh, I see. That makes sense. Okay, now for the dares."

He looked relieved when she said those words. "Great! What can I do to earn my freedom?"

"You have to kiss me twice." He stared blankly at her for a few seconds before realizing what she meant. His eyes widened noticeably, and he stammered, "but... but Mistress!"

She rolled her eyes. "You agreed to these terms already, remember? You should have known better than to expect something different."

His mouth opened and closed several times before he finally nodded slowly. "Yes ma'am."

As soon as they were standing together, she grabbed his head firmly between her hands and pulled his lips against hers. At first he resisted, trying desperately to avoid eye contact even though she held his gaze directly. However, after a moment he gave in completely and kissed her passionately.

When she broke their embrace, she saw that he appeared flushed and breathing rapidly. It made her smile. "Good job!" she exclaimed. "Now let's try again."

This time, she led him over to the bed where she pushed him down onto his knees. Then she straddled his body, facing his feet, and leaned forward to press her breasts into his back. As she began grinding against him, she whispered into his ear, "I bet you wish you had more control right now, huh? Maybe you'd rather be fucking me right now instead of being forced to take whatever I want from you."

He moaned loudly in response, unable to stop himself despite knowing full well that she might punish him later.

After several minutes of teasing him mercilessly, she finally allowed herself to come. When she collapsed beside him on the mattress, he turned around eagerly to look at her. Seeing her satisfied expression, he reached out tentatively towards her crotch. Before he could touch her, however, she stopped him.

"Now is not the time, Benjamin. We still have another dare left."

"But... but we finished our game last night," he protested weakly. "Can't I please get some relief today?" The desperation in his voice almost made her relent; however, she knew that giving in wouldn't help either of them in the long run.

Instead, she stood quickly and walked over to her suitcase. From inside she retrieved a small black box containing a metal chastity device. She placed it gently on top of the dresser across the room from where he lay panting on the floor.

"What is that?" he asked quietly.

"It's called a cock cage," she replied simply.

Without waiting for further questions, she approached him and knelt down next to him. "Stand up, Benjamin." Once he obeyed, she slid the device carefully over his erect member. Despite its size, it fit snugly without causing discomfort.

Then she fastened the lock securely behind his ballsack, leaving him trapped within the confines of the steel contraption. Finally, she attached a chain to one end of the device and secured it to the leg of the bed frame.

"Okay, Ben," she said calmly. "Twenty four hours from now, I'll unlock you if you manage to complete your second task successfully. Until then, enjoy your stay here."

With that, she headed toward the bathroom to shower once again while he remained bound and helpless on the floor.

The sound of running water filled the room until she emerged wearing nothing but a towel wrapped tightly around her waist. Her hair was wet and dripping down her shoulders, making her appear younger and less intimidating somehow.

Seeing her approach, he tried to sit up, but found that the angle prevented him from doing anything other than lie flat on his stomach. He struggled briefly before resigning himself to his fate.

Erica smiled slightly at his efforts. "Don't worry, Ben. I won't leave you like this forever. Just think of it as an opportunity to rest and recover from yesterday's activities."

She sat down on the edge of the bed near him and watched him closely. After several moments passed silently, she spoke again. "Do you know how much I enjoyed watching you struggle last night?"

He shook his head no, clearly too embarrassed to admit otherwise.

"Well, I did. Every little twitch of your muscles told me just how hard you were working to satisfy me. And every noise you made -- whether it came from pleasure or pain -- made me feel powerful beyond belief.